Benzoic acid ester of m-(2-propynyloxy)phenol



dfildflh Patented Apr. l8, 19f

3,314,986 BENZOIC ACID ESTER 01F M-(l-PRQ- PYNYLUXYWHENOL Chester E. Pawloslti, Bay tlity, Mich, assignor to The Dow Chemical Company, Midland, Mich, a corporation of Delaware No Drawing. Filed Dec. 26, 1963, Ser. No. 333,756 1 Claim. (Cl. 260-476) The present invention is directed to m-(Lpropynyloxy) phenyl benzoate corresponding to the formula 10 GHzCECH This compound is a liquid which is somewhat soluble in many organic solvent-s and of low solubility in Water. The compound has been found to be useful as a parasiticide for the control of various insect, worm, bacterial, fungal and mite organisms such as tapeworms, round- Worms, roaches and plant blight.

The compound can be prepared by reacting resorcinol monobenzoate and a propargyl halide such as propargyl romide Or propargyl chloride. The reaction is carried out in the presence of a basic material and preferably in a liquid reaction medium such as isopropanol, acetone or methyl ethyl ketone. The reaction takes place smoothly in the temperature range at which the halide of reaction is formed and preferably between the temperatures of and 100 C. The halide of reaction appears in the reaction mixture as the salt of the metal cation of the employed base. The amounts of the reactants to be employed are not critical, some of the desired product being obtained when employing the reactants in any amounts. However, the reaction consumes the reactants in equimolar proportions and the use of amounts which represent such proportions is preferred. Upon completion of the reaction the desired product can be separated and purified by conventional procedures.

In carrying out the reaction the propargyl halide and the resorcinol monobenzoate and the basic material are combined in any convenient fashion, however, in a preferred method they are dispersed in an organic solvent as reaction medium. The resulting mixture is elevated to and maintained at the reaction temperature until there is a subsantial cessation in the formation of the halide reaction. The reaction mixture can then be filtered a1 employed in pesticidal compositions. In a preferred pr cedure the reaction mixture is combined with an aqueo solution of alkali metal hydroxide and the mixture heat for a short time. The reaction mixture is then WElSllt with water. The organic layer which is obtained durii the washing procedure is collected. and heated to remo any low boiling constituents and obtain the desired pro uct as a liquid residue.

In a representative operation resorcinol monobenzoa (75 grams), propargyl bromide grams) and pota sium carbonate grams) were dispersed in 500 mil] liters of acetone and the resulting mixture heated at tl boiling temperature and under reflux for 24 hours. T the reaction mixture was added an aqueous solution of "2 percent sodium hydroxide and the mitxure heated ft another 4 hours. At the end of the heating period tl reaction mixture was Washed with water and the organ: layer Which separated during the washing procedure WE heated to remove the low boiling constituents. As a It sult of these operations, there was obtained the m-(Z-prx pynyloxy)phenyl benzoate product as a liquid residu having a refractive index n/D of 1.5563 at 25 C.

The novel product of the present invention is useful a the toxic constituent in pesticidal applications for the cor trol of the growth and killing of a number of insect, mite Worm, bacterial, plant and fungal organisms. For sucI uses, the product can be dispersed on an inert finely di vided solid and employed as a dust. Such mixtures ma also be dispersed in water with or without the aid of surface active agent and the resulting aqueous suspension employed as sprays. In other procedures, the product i employed as an active constituent in solvent solutions, oil in-Water or Water-inoil emulsions or aqueous dispersions In representative operations, finely divided solid composi tions containing 600 parts per million by weight of m-(Z propynyloxy)phenyl benzoate gives percent kills 0 mouse pinworms and mouse tapeworms.

I claim:

m (2-propynyloxy) phenyl benzoate.

No references cited.

LORRAINE A. WEINBERGER, Primary Examiner. T. GALLOWAY, Assistant Examiner 

